Dyestuff of the anthraquinone series and process of making same



Patented Mar. 2, 1926.

UNITED sTATEs PATENT OFFICE,

sums BLDDIL'EY AND WILLIAM WYNDHAIMI TATUM, F MANCHESTER, ENGLAND,ASSIGHOBS TO BRITISH DYESTUFFS CORPORATION LIMITED, OF MANCHESTER,

ENGLAND.

I I0 Drawing.

' densed with a sulphochloro derivative of salicylic acid,

C,H .CO H.OH.SO, Cl, which may be here called the sul ho chloride orsalicyhc acid or salicylic sulp o chloride.

They have most probably the general formula:

in which A represents an anthraquinone residue,- which may be suitablysubstituted linked by .NH. to the sulpho chloride mmdue. The newdyestuffs posses in general acidic properties and dye wool directly inbright even shades of remarkablefastness to milling and washing. Thedyes in addition I ssess' mordan't properties and may be 85 appliedaccording to the methods generally in use in this branch, i. e., theymay bev dyed on achorme mordant or may be afterchromed or may be (1 ed bthe metachrome process. The chrome sha es are extraordinarily fast 40 tomilling and potting and possess the great advantage that they arenotdgreatly difierent in hue from the unchrom shades. The new dyes mayalso be used in calico printing being applied to the fibre wlth amordant e. g., chromium aceta accor the conventional methods in art, anin dyeing aceilryl silk; that silk made from acetyl cell ose orcellulose acetate, as it is sometimes called.

The follo examples will serve to illustrate further he nature of theinvention, but the invention is not confined to examples:

' OF THE ANTERAQUINONE SERIES AND PROCESS OF MAKING SAME.

Application filed April 18, 1923. Serial No. 682,988.

E sample 1.

A mixture consisting of 10 parts of diis heated at100 C. until nofurther re action takes place. The nitrobenzene is then removed by steamdistilling the mixture in the presence of a slight excess of sodiumcarbonate. The residue is an aqueous solution of the new dyestufi in theform of its sodium salt. The colour may. be isolated in a state ofpurity by filterin the solution from any alkali-insoluble products andprecipitating it in the form of free acid by the use of hydrochloricacid. It may be converted to its sodium salt in the usual way. Thesodium salt is easily soluble in water and dyes wool from an aciddyebath in reddish blue shades which are remarkably fast to alkalinemilling. One afterchroming the shade becomes greener in hue and is fastto mi and potting. When rinted on calico with chromium acetate Incshades fast to soaping are produced.

Acetyl silk is dyed a blue shade.

' Example 2.

10 parts of 1.4 diaminoanthraquinone are condensed with ll parts ofsalicylic sulpho chloride in 72 parts of nitrobenzene at 60- C. When thereaction iscomplete the new dyestufl' is mainly out of solution. It isfiltered ofi, freed from nitrobenzene by steaming and worked up asbefore. The new dyestufi' forms an easily soluble sodium salt and dyeslevel shades of bluish-red in the acid dyebath. The direct dyeingswithstand alkaline milling. On afterchroming they are almost unchangedin hue but become rather faster to alkine milling and fast to potting.When rinted on cotton with" chromium acetate in the usual way bluish-redprints are obtained which are fast to soa ing. Acetyl silk is d ed abluish-red o extraordinarily fine sha e and fastness.

Example 3.

Dyeatu/f from 1:4:5:8-tetm-amino aw thraquinone and salicylic aulphochloride.-

parts tetra-amino anthr uinone, 25 arts salicylic aulpho chloride, 1 im.

goes into solution with a beautifu blue colour. The solution is filteredfrom any insoluble mailer and precipitated by addi-v tion of salt. Thenew dyestufi dyes wool in bright blue shades having very good fastnessproperties. It also has a good aflinity for acetyl silk dyeing the fibrein fast blue shades.

Now what we claim is 1. The new dyestuffs of the anthraquinone series ofthe general formula awn-e000 in which A represents an anthraquinoneresidue, which can be suitably substituted, which are acid dyestuffsdyeing wool directly and also dye on a'chrome mordant" and possessconsiderable aflinity for acetyl A-NH-SO O H thraquinone residue, saiddyestufi bein an acidic dycstufi', which in the forni 0 its sodium saltis soluble in water, dyes wool from the acid bath giving bluish-redshades, which .is almost unchanged in shade on after-chromin and whichdyes acetyl silk :1 bluish-red shade. Y

. 3. The process of manufacturing new dyestufi's of the anthraquinoneseries which comprises condensing an amino derivative of anthraquinonewith the sulpho chloride of salicylic acid. H

In testimony whereof, we have hereunto affixed our si natures.

JAME BADDILEY. \VILLI-AM WYNDHAM TATUM.

' in which A represents a 1.4 diamino an-

